Sailing in Key West, FL

Sail Key West waters on a private 4-hour charter for up to six guests

Charter a private historic schooner sail with drinks and snacks included

Sail the Florida Keys privately aboard a classic sailboat

Settle into a classic schooner for an intimate Key West sunset

Private catamaran sailing with champagne, wines and a gourmet cheese buffet

Stretch out and relax on a private sail

Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset

Sail, snorkel, and seek sandbars aboard a private catamaran

Learn sailing fundamentals aboard Hobie Wave catamarans

Sail a 1939 wooden schooner and take a turn at the helm

Private Key West harbor sail with time at the helm

Sail beyond Key West for snorkeling, kayaking, fishing and lunch

Toast the sunset with champagne aboard a private 47-foot sloop

Spend a full day sailing from Key West with up to 6 guests

Private catamaran sailing for sunrise or sunset ocean views

Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included

Private Key West sailing with snorkeling, sandbars, and dolphin searches

Sail, snorkel, and explore Key West waters on your private catamaran

Take your Fantasy Fest day to the water with a sandbar stop and floating gear

Private sunset sailing with bubbly, wines and a gourmet cheese buffet

Private sailing with an onboard bathroom and kitchen

Sail Key West’s Atlantic coast at sunset aboard a historic schooner

Sail the ocean in privacy with a full bathroom and kitchen onboard

Make sunset your own with a private schooner sail